Amino nitrites are organic compounds that have at least one amino group and at least one nitrile group. Amino nitriles have been found to be useful starting materials and intermediates for the production of fine chemicals.
One route for the production of amino nitrites is disclosed in Caputo et al, “Synthesis of Enantiopure N- and C-Protected homo-β-Amino Acids by Direct Homologation of the α-Amino Acids”, Tetrahedron Letters, Vol. 51, No. 45, pp. 123337-12350, 1995. Caputo discloses the use of a triarylphosphine-iodine polymer bound complex in the presence of imidazole to replace the hydroxyl group with the iodo group and the subsequent displacement of the iodo group with a cyanide. The introduction of polymer bound reactants makes this methodology costly and undesirable. Moreover, Caputo utilized tetraethylammonium cyanide as a nucleophilic reagent and experienced significant deprotection of the amino group.
Another reaction scheme disclosed in Toujas, et al., Synthesis of homochiral N-Boc-β-aminoaldehydes from N-Boc-β-aminonitriles, Bull. Soc. Chim. Fr. (1997), 134(7), 713-717 utilizes costly solvents and results in low yields. Toujas, et al., discloses the N-Boc protection of the amino group and mesylation of the hydroxyl with methanesulfonyl chloride in the presence of triethylamine at room temperature. According to Toujas, et al., nucleophilic substitution with sodium cyanide in DMSO gives a relatively low yield of 56%.
The existing processes for producing useful amino nitrites have proven to be inefficient as multi steps are required and low yields are normally obtained.